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Lexical ambiguities and pragmatic issues represent major concerns for Saudi EFL learners’ dictionary use preferences. These concerns have been often reflected when students are requested to translate texts embedded with polysemous, homonymous, and pejorative lexical items, which are extensively used in Arabic texts. Therefore, the present study aims to examine the lexical and pragmatic issues impeding Saudi EFL learners from the better use of dictionaries especially when translating texts from Arabic to English. The present study uses the contextual variability of meaning of Cruse (2000) as its approach assuming that the meaning of a particular word can vary from context to context. A number of 39 Saudi EFL learners in Saudi University were asked to translate some short Arabic passages from Arabic to English, which include several lexical and pragmatic issues like polysemy, semantic change, dialectal issues, pejorative and ameliorative meanings, tonal register and social registers and so on. The study reveals that Saudi EFL learners demonstrate preferences for literal equivalence over dynamic and free equivalent. In addition, they are often unaware of lexical and pragmatic issues relating to the meaning that may hinder the correct application of dictionary information. This study recommends that EFL learners have to be informed about the dictionary use behavior while studying translation courses.